A new portrait of the founding father challenges the long-held perception of Thomas Jefferson as a benevolent slaveholder

After the violent tenures of earlier overseers, Gabriel Lilly seemed to portend a gentler reign when he arrived at Monticello in 1800. Colonel Randolph’s first report was optimistic. “All goes well,” he wrote, and “what is under Lillie admirably.” His second report about two weeks later was glowing: “Lillie goes on with great spirit and complete quiet at Mont’o.: he is so good tempered that he can get twice as much done without the smallest discontent as some with the hardest driving possible.” In addition to placing him over the laborers “in the ground” at Monticello, Jefferson put Lilly in charge of the nailery for an extra fee of £10 a year.

Once Lilly established himself, his good temper evidently evaporated, because Jefferson began to worry about what Lilly would do to the nailers, the promising adolescents whom Jefferson managed personally, intending to move them up the plantation ladder. He wrote to Randolph: “I forgot to ask the favor of you to speak to Lilly as to the treatment of the nailers. it would destroy their value in my estimation to degrade them in their own eyes by the whip. this therefore must not be resorted to but in extremities. as they will again be under my government, I would chuse they should retain the stimulus of character.” But in the same letter he emphasized that output must be maintained: “I hope Lilly keeps the small nailers engaged so as to supply our customers.”

Colonel Randolph immediately dispatched a reassuring but carefully worded reply: “Everything goes well at Mont’o.—the Nailers all [at] work and executing well some heavy or­­­­­­­­­­­­ders. ...I had given a charge of lenity respecting all: (Burwell absolutely excepted from the whip alltogether) before you wrote: none have incurred it but the small ones for truancy.” To the news that the small ones were being whipped and that “lenity” had an elastic meaning, Jefferson had no response; the small ones had to be kept “engaged.”

It seems that Jefferson grew uneasy about Lilly’s regime at the nailery. Jefferson replaced him with William Stewart but kept Lilly in charge of the adult crews building his mill and canal. Under Stewart’s lenient command (greatly softened by habitual drinking), the nailery’s productivity sank. The nail boys, favored or not, had to be brought to heel. In a very unusual letter, Jefferson told his Irish master joiner, James Dinsmore, that he was bringing Lilly back to the nailery. It might seem puzzling that Jefferson would feel compelled to explain a personnel decision that had nothing to do with Dinsmore, but the nailery stood just a few steps from Dinsmore’s shop. Jefferson was preparing Dinsmore to witness scenes under Lilly’s command such as he had not seen under Stewart, and his tone was stern: “I am quite at a loss about the nailboys remaining with mr Stewart. they have long been a dead expence instead of profit to me. in truth they require a vigour of discipline to make them do reasonable work, to which he cannot bring himself. on the whole I think it will be best for them also to be removed to mr Lilly’s [control].”

The incident of horrible violence in the nailery—the attack by one nail boy against another—may shed some light on the fear Lilly instilled in the nail boys. In 1803 a nailer named Cary smashed his hammer into the skull of a fellow nailer, Brown Colbert. Seized with convulsions, Colbert went into a coma and would certainly have died had Colonel Randolph not immediately summoned a physician, who performed brain surgery. With a trephine saw, the doctor drew back the broken part of Colbert’s skull, thus relieving pressure on the brain. Amazingly, the young man survived.

Bad enough that Cary had so viciously attacked someone, but his victim was a Hemings. Jefferson angrily wrote to Randolph that “it will be necessary for me to make an example of him in terrorem to others, in order to maintain the police so rigorously necessary among the nail boys.” He ordered that Cary be sold away “so distant as never more to be heard of among us.” And he alluded to the abyss beyond the gates of Monticello into which people could be flung: “There are generally negro purchasers from Georgia passing about the state.” Randolph’s report of the incident included Cary’s motive: The boy was “irritated at some little trick from Brown, who hid part of his nailrod to teaze him.” But under Lilly’s regime this trick was not so “little.” Colbert knew the rules, and he knew very well that if Cary couldn’t find his nailrod, he would fall behind, and under Lilly that meant a beating. Hence the furious attack.

Jefferson’s daughter Martha wrote to her father that one of the slaves, a disobedient and disruptive man named John, tried to poison Lilly, perhaps hoping to kill him. John was safe from any severe punishment because he was a hired slave: If Lilly injured him, Jefferson would have to compensate his owner, so Lilly had no means to retaliate. John, evidently grasping the extent of his immunity, took every opportunity to undermine and provoke him, even “cutting up [Lilly’s] garden [and] destroying his things.”

But Lilly had his own kind of immunity. He understood his importance to Jefferson when he renegotiated his contract, so that beginning in 1804 he would no longer receive a flat fee for managing the nailery but be paid 2 percent of the gross. Productivity immediately soared. In the spring of 1804, Jefferson wrote to his supplier: “The manager of my nailery had so increased its activity as to call for a larger supply of rod...than had heretofore been necessary.”

Maintaining a high level of activity required a commensurate level of discipline. Thus, in the fall of 1804, when Lilly was informed that one of the nail boys was sick, he would have none of it. Appalled by what happened next, one of Monticello’s white workmen, a carpenter named James Oldham, informed Jefferson of “the Barbarity that [Lilly] made use of with Little Jimmy.”

Oldham reported that James Hemings, the 17-year-old son of the house servant Critta Hemings, had been sick for three nights running, so sick that Oldham feared the boy might not live. He took Hemings into his own room to keep watch over him. When he told Lilly that Hemings was seriously ill, Lilly said he would whip Jimmy into working. Oldham “begged him not to punish him,” but “this had no effect.” The “Barbarity” ensued: Lilly “whipped him three times in one day, and the boy was really not able to raise his hand to his head.”

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